Natural Product: NPC477199

Natural Product ID:  NPC477199
Common Name:   Gracilamide A
IUPAC Name:   (2R)-N-[(E,2S,3S,4R)-11-(2-butylcyclopropyl)-1,3,4-trihydroxyundec-6-en-2-yl]-2-hydroxypentacosanamide
Synonyms:  
Molecular Formula:   C43H83NO5
Standard InCHIKey:  MFPIKADAVWYTIK-SVZYJHTQSA-N
Standard InCHI:  InChI=1S/C43H83NO5/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-26-30-34-41(47)43(49)44-39(36-45)42(48)40(46)33-29-27-24-25-28-32-38-35-37(38)31-6-4-2/h27,29,37-42,45-48H,3-26,28,30-36H2,1-2H3,(H,44,49)/b29-27+/t37?,38?,39-,40+,41+,42-/m0/s1
Canonical SMILES:  CCCCCCCCCCCCCCCCCCCCCCC[C@H](C(=N[C@H]([C@@H]([C@@H](C/C=C/CCCCC1CC1CCCC)O)O)CO)O)O
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO10746 Gracilaria asiatica Species Gracilariaceae Eukaryota PMID[17067168]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified Activity = 11.7 % 17067168

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC477199 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.8846 High Similarity NPC264417
0.8846 High Similarity NPC217095
0.8333 Intermediate Similarity NPC477200
0.8298 Intermediate Similarity NPC477198
0.8025 Intermediate Similarity NPC288086
0.7949 Intermediate Similarity NPC195165
0.7674 Intermediate Similarity NPC207657
0.7531 Intermediate Similarity NPC103712
0.7531 Intermediate Similarity NPC291196
0.7416 Intermediate Similarity NPC228638
0.7391 Intermediate Similarity NPC316186
0.734 Intermediate Similarity NPC61894
0.734 Intermediate Similarity NPC475603
0.7308 Intermediate Similarity NPC145627
0.7241 Intermediate Similarity NPC474833
0.7128 Intermediate Similarity NPC39290
0.7128 Intermediate Similarity NPC159369
0.7093 Intermediate Similarity NPC140327
0.7093 Intermediate Similarity NPC212008
0.7093 Intermediate Similarity NPC51055
0.7093 Intermediate Similarity NPC62293
0.7059 Intermediate Similarity NPC314678
0.7051 Intermediate Similarity NPC329003
0.7051 Intermediate Similarity NPC325550
0.7051 Intermediate Similarity NPC326524
0.7041 Intermediate Similarity NPC475503
0.6923 Remote Similarity NPC321030
0.6869 Remote Similarity NPC189629
0.6837 Remote Similarity NPC262312
0.6837 Remote Similarity NPC70323
0.6837 Remote Similarity NPC17290
0.6837 Remote Similarity NPC3568
0.6837 Remote Similarity NPC192066
0.6837 Remote Similarity NPC23454
0.6837 Remote Similarity NPC35269
0.6837 Remote Similarity NPC256570
0.6813 Remote Similarity NPC82799
0.6804 Remote Similarity NPC263545
0.6804 Remote Similarity NPC309898
0.6804 Remote Similarity NPC186840
0.6804 Remote Similarity NPC282705
0.6804 Remote Similarity NPC473950
0.6804 Remote Similarity NPC475125
0.6804 Remote Similarity NPC15851
0.6804 Remote Similarity NPC473581
0.6804 Remote Similarity NPC111567
0.6804 Remote Similarity NPC473604
0.6804 Remote Similarity NPC182632
0.68 Remote Similarity NPC475646
0.6747 Remote Similarity NPC113224
0.6739 Remote Similarity NPC474312
0.6731 Remote Similarity NPC74035
0.6705 Remote Similarity NPC3094
0.6701 Remote Similarity NPC209047
0.6701 Remote Similarity NPC74672
0.6701 Remote Similarity NPC242503
0.6701 Remote Similarity NPC139782
0.6701 Remote Similarity NPC43074
0.67 Remote Similarity NPC183449
0.67 Remote Similarity NPC197294
0.67 Remote Similarity NPC8098
0.67 Remote Similarity NPC45313
0.6667 Remote Similarity NPC156782
0.6667 Remote Similarity NPC158445
0.6667 Remote Similarity NPC225978
0.6667 Remote Similarity NPC34754
0.6667 Remote Similarity NPC475918
0.6667 Remote Similarity NPC206711
0.6667 Remote Similarity NPC271207
0.6667 Remote Similarity NPC29501
0.6667 Remote Similarity NPC255175
0.6667 Remote Similarity NPC282088
0.6667 Remote Similarity NPC54961
0.6667 Remote Similarity NPC157353
0.6635 Remote Similarity NPC476877
0.6627 Remote Similarity NPC474402
0.6596 Remote Similarity NPC476523
0.6574 Remote Similarity NPC113012
0.6574 Remote Similarity NPC122926
0.6571 Remote Similarity NPC88267
0.6571 Remote Similarity NPC113326
0.6571 Remote Similarity NPC194390
0.6571 Remote Similarity NPC224610
0.6538 Remote Similarity NPC242930
0.6509 Remote Similarity NPC476876
0.6484 Remote Similarity NPC469492
0.6471 Remote Similarity NPC240650
0.6463 Remote Similarity NPC47333
0.6413 Remote Similarity NPC469517
0.6408 Remote Similarity NPC234542
0.6395 Remote Similarity NPC474812
0.6389 Remote Similarity NPC307903
0.6389 Remote Similarity NPC140251
0.6386 Remote Similarity NPC477106
0.6383 Remote Similarity NPC39966
0.6375 Remote Similarity NPC52012
0.6355 Remote Similarity NPC154601
0.6355 Remote Similarity NPC258130
0.6353 Remote Similarity NPC315141
0.6353 Remote Similarity NPC129995
0.6346 Remote Similarity NPC473224
0.6344 Remote Similarity NPC79367
0.6337 Remote Similarity NPC473314
0.6337 Remote Similarity NPC280710
0.6337 Remote Similarity NPC243985
0.6321 Remote Similarity NPC45365
0.6321 Remote Similarity NPC293299
0.6296 Remote Similarity NPC475800
0.6289 Remote Similarity NPC258824
0.6283 Remote Similarity NPC172197
0.6283 Remote Similarity NPC274293
0.6282 Remote Similarity NPC270041
0.6265 Remote Similarity NPC29468
0.625 Remote Similarity NPC477793
0.625 Remote Similarity NPC329919
0.6239 Remote Similarity NPC469943
0.6239 Remote Similarity NPC70235
0.6235 Remote Similarity NPC477525
0.6226 Remote Similarity NPC50815
0.6226 Remote Similarity NPC247060
0.6222 Remote Similarity NPC86064
0.622 Remote Similarity NPC122239
0.6216 Remote Similarity NPC476875
0.6211 Remote Similarity NPC477730
0.6211 Remote Similarity NPC224072
0.6204 Remote Similarity NPC201128
0.6195 Remote Similarity NPC50694
0.619 Remote Similarity NPC316674
0.6182 Remote Similarity NPC473578
0.6182 Remote Similarity NPC474725
0.618 Remote Similarity NPC474403
0.6168 Remote Similarity NPC474583
0.6162 Remote Similarity NPC470284
0.6161 Remote Similarity NPC478024
0.6145 Remote Similarity NPC130807
0.6139 Remote Similarity NPC314500
0.6125 Remote Similarity NPC281590
0.6118 Remote Similarity NPC253468
0.6118 Remote Similarity NPC235311
0.6111 Remote Similarity NPC476709
0.6111 Remote Similarity NPC43219
0.6111 Remote Similarity NPC305223
0.6111 Remote Similarity NPC14537
0.6098 Remote Similarity NPC226848
0.6092 Remote Similarity NPC73603
0.6092 Remote Similarity NPC163290
0.6091 Remote Similarity NPC207820
0.6091 Remote Similarity NPC475150
0.6087 Remote Similarity NPC201968
0.6075 Remote Similarity NPC471083
0.6058 Remote Similarity NPC175614
0.6055 Remote Similarity NPC473252
0.6055 Remote Similarity NPC271269
0.6055 Remote Similarity NPC472615
0.6053 Remote Similarity NPC472536
0.6053 Remote Similarity NPC471645
0.6053 Remote Similarity NPC103391
0.6044 Remote Similarity NPC471525
0.6042 Remote Similarity NPC477390
0.6042 Remote Similarity NPC477385
0.604 Remote Similarity NPC477866
0.604 Remote Similarity NPC477865
0.6022 Remote Similarity NPC476703
0.6019 Remote Similarity NPC474563
0.6019 Remote Similarity NPC241879
0.6018 Remote Similarity NPC279383
0.6018 Remote Similarity NPC261750
0.6018 Remote Similarity NPC268327
0.6018 Remote Similarity NPC1111
0.6018 Remote Similarity NPC469865
0.6018 Remote Similarity NPC295444
0.6018 Remote Similarity NPC273215
0.6017 Remote Similarity NPC315188
0.6 Remote Similarity NPC4834
0.6 Remote Similarity NPC471023
0.6 Remote Similarity NPC55068
0.6 Remote Similarity NPC251330
0.6 Remote Similarity NPC140300
0.6 Remote Similarity NPC473501
0.6 Remote Similarity NPC475439
0.5982 Remote Similarity NPC251122
0.5981 Remote Similarity NPC474873
0.5977 Remote Similarity NPC272125
0.5977 Remote Similarity NPC311736
0.5977 Remote Similarity NPC267027
0.5976 Remote Similarity NPC472578
0.5976 Remote Similarity NPC302569
0.5976 Remote Similarity NPC168308
0.5966 Remote Similarity NPC273185
0.5963 Remote Similarity NPC472616
0.5962 Remote Similarity NPC119225
0.5962 Remote Similarity NPC25033
0.5962 Remote Similarity NPC476261
0.5962 Remote Similarity NPC58674
0.5962 Remote Similarity NPC471635
0.5962 Remote Similarity NPC470382
0.596 Remote Similarity NPC477728
0.5957 Remote Similarity NPC473972
0.5957 Remote Similarity NPC473971
0.5957 Remote Similarity NPC475363

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC477199 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.7143 Intermediate Similarity NPD3187 Discontinued
0.6729 Remote Similarity NPD6421 Discontinued
0.6701 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6566 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6509 Remote Similarity NPD5357 Phase 1
0.631 Remote Similarity NPD1831 Phase 3
0.6273 Remote Similarity NPD6420 Discontinued
0.6055 Remote Similarity NPD6640 Phase 3
0.6 Remote Similarity NPD3210 Clinical (unspecified phase)
0.5932 Remote Similarity NPD2217 Approved
0.5932 Remote Similarity NPD2218 Phase 2
0.5905 Remote Similarity NPD4228 Discovery
0.5833 Remote Similarity NPD4760 Clinical (unspecified phase)
0.5812 Remote Similarity NPD7505 Discontinued
0.581 Remote Similarity NPD4814 Discontinued
0.5804 Remote Similarity NPD6406 Approved
0.5789 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5789 Remote Similarity NPD7918 Clinical (unspecified phase)
0.5789 Remote Similarity NPD7917 Clinical (unspecified phase)
0.5789 Remote Similarity NPD3732 Approved
0.5778 Remote Similarity NPD1082 Approved
0.5778 Remote Similarity NPD791 Approved
0.5778 Remote Similarity NPD15 Approved
0.5763 Remote Similarity NPD7641 Discontinued
0.5752 Remote Similarity NPD6413 Approved
0.5747 Remote Similarity NPD277 Approved
0.5728 Remote Similarity NPD3168 Discontinued
0.5728 Remote Similarity NPD7838 Discovery
0.5714 Remote Similarity NPD3212 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7522 Discontinued
0.5714 Remote Similarity NPD5771 Approved
0.567 Remote Similarity NPD4820 Approved
0.567 Remote Similarity NPD4821 Approved
0.567 Remote Similarity NPD4822 Approved
0.567 Remote Similarity NPD4819 Approved
0.5656 Remote Similarity NPD7829 Approved
0.5656 Remote Similarity NPD7830 Approved
0.5652 Remote Similarity NPD1719 Phase 1
0.5625 Remote Similarity NPD4268 Approved
0.5625 Remote Similarity NPD4211 Phase 1
0.5625 Remote Similarity NPD4271 Approved
0.5625 Remote Similarity NPD4738 Phase 2
0.562 Remote Similarity NPD8444 Approved
0.561 Remote Similarity NPD8342 Approved
0.561 Remote Similarity NPD8299 Approved
0.561 Remote Similarity NPD8341 Approved
0.561 Remote Similarity NPD8340 Approved
0.5607 Remote Similarity NPD3190 Approved
0.5607 Remote Similarity NPD3191 Approved
0.5607 Remote Similarity NPD3189 Approved

Structure

External Identifiers

PubChem CID   16059816
ChEMBL   CHEMBL506524
ZINC  

Physicochemical Properties

Molecular Weight:  693.63
ALogP:  -8.7766
MLogP:  5.53
XLogP:  16.605
# Rotatable Bonds:  44
Polar Surface Area:  113.51
# H-Bond Aceptor:  6
# H-Bond Donor:  5
# Rings:  1
# Heavy Atoms:  49

Download Data

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Structure MOL file  
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Similar NPs/Drugs